Vacation rentals with a pool in Tobago

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Tobago

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

The hallway showcases a wooden sign reading 'IVB Buccoo Place' on a white wall. A sliding barn door is positioned to the right, leading to a living area. Neutral-toned flooring extends throughout, leading to a cozy seating arrangement with cushions in warm colors visible in the distance.

Apartment in Buccoo

4.97 out of 5 average rating, 38 reviews

Guest Favourite - The Balcony, 4B Buccoo, 2BR Apt

Explore our stylish condo in Buccoo, with onsite restaurants and a coffee shop, just 7 minutes drive from Buccoo Bay, 10 minutes from Grafton and Mt Irvine beaches and Golf Course. Approx 15 minutes from Pigeon Pt and Store Bay beaches. Surf enthusiastsExperience modern comfort, strategically placed for effortless exploration of Tobago's treasures; Nylon Pool, Argyle Waterfall, scenic drive through the rain forest to list a few. Sea Horse, Waves and Fish Pot restaurants all within 10 mins drive!

Top guest favorite

An infinity pool reflects the sky, surrounded by a wooden deck and tropical foliage. Sun loungers under large umbrellas are positioned nearby. The villa structure features elegant overhangs, promoting natural light and providing shaded areas for relaxation.

Apartment in Bethel

4.99 out of 5 average rating, 129 reviews

Firefly Villa - 'Roots'

A spacious, modern, beautifully decorated home with a zen vibe and an inspiring location for working away from home. ‘Roots’ has two cozy double bedrooms, comfortable work spaces and fully-equipped kitchen with kitchen island, and deluxe double fronted fridge, en-suite bathrooms and wooden floors. Lie by the infinity pool and watch as a bright blue-grey tanager flies right over your head from one tree to the next. The perfect blend of treehouse and charming, stylish Caribbean poolside villa.

Guest favorite

Villa in Lowlands

4.91 out of 5 average rating, 45 reviews

Villa Yemanjá

Named after the Brazilian goddess of the sea, Yemanjá is a luxurious oceanfront villa located in the prestigious Tobago Plantations Estate. The colonial style architecture of the villa is enhanced by a lush landscaped tropical garden. Balinese inspired decor soothes the senses. The property features four en-suite bedrooms, a double bed loft and a maid’s quarters, comfortably sleeping 11. A spaciously covered patio opens out onto an infinity swimming pool, heated Jacuzzi and pebble beach.

Guest favorite

A swimming pool area is surrounded by lush greenery, featuring a large pool and a smaller hot tub. Two striped lounge chairs are positioned nearby on a grassy area, complemented by potted plants that add to the serene atmosphere.

Apartment in Western Tobago

4.82 out of 5 average rating, 77 reviews

Pool View Apartment. Close to everything!!!

Be COVID Free! Have a fear of contracting COVID whilst on vacation?Then this is the correct accommodation for you! Spacious, modern, elegantly decorated studio. Close to all major sites and attractions but away from overly crowded spaces. Apartment is equipped with a queen sized bed, sofa, smart tv, large bathroom, fully equipped kitchen, hot water, wifi, swimming pool and much more! Ideal for short or long term stays and for couples looking for time away. Come enjoy relaxation in style.

Superhost

A contemporary villa exterior is showcased, featuring a saltwater pool bordered by lounge chairs. The poolside cabana bar is visible in the background, framed by lush greenery and a clear blue sky.

Villa in Tobago

4.8 out of 5 average rating, 92 reviews

Nirvana Tobago Villa Saltwater Pool & Ocean View

Nirvana Tobago is a luxurious Private Villa on the Caribbean coast with Ocean Views. Ample alfresco dining space, poolside cabana bar and saltwater pool. Over 4000+ sq. ft residence is graced with 12-foot ceilings and skylights. Interiors feature a chef kitchen and well-appointed bedrooms with ensuite bathrooms, no better place to restore your sense of bliss! Perfect for weekend getaways, extended stays and remote working. We have fast and reliable wifi and laptop friendly workspaces.

Superhost

A shaded pool area features a spacious in-ground pool with calm blue waters, accented by a rock feature. Two lounge chairs are positioned beside the pool, while panoramic sea views and lush greenery surround the space, creating a serene outdoor environment.

Home in Castara

4.81 out of 5 average rating, 27 reviews

The Wood House

The Wood House is a beautiful, secluded, open-plan cottage with spectacular sea views, a natural setting in a reclaimed woodland, and close proximity to Englishman’s Bay (considered one of the 10 most beautiful beaches in the Caribbean). The natural woodland attracts a large variety of wildlife making it ideal for birders or naturalists interested in exploring the Tobago environment. Walk the terraced grounds, explore Englishman's Bay estate, or just relax in the stunning views.

Guest favorite

Villa in Hope estates

4.93 out of 5 average rating, 15 reviews

"Malibu" in Tobago at the Ocean's Edge!

Think 'Malibu in Tobago' and you will know what it feels like to be welcomed into this luxurious penthouse villa at the ocean's edge. This stunning 3-bdrm villa located in Hope Estate, about a 10-min drive from the port in Scarborough, offers an unparalleled oceanfront experience with breathtaking views of the Atlantic and a salt water pool to make Malibu an even more enticing choice. All rooms are air-conditioned and minimally, yet beautifully, appointed with an ocean view.

Guest favorite

The outdoor area features a private pool surrounded by a spacious deck. Two lounge chairs are positioned beside the pool, while the house's exterior showcases large windows and a modern roof design. Lush greenery is visible in the background, adding to the tranquil environment.

Home in Bon Accord

4.92 out of 5 average rating, 110 reviews

La Casa de Serenidad, Juego & Familia

This place is perfect for a small or relatively large group. It is equipped with a fully-functional modern-styled kitchen, a spacious communal area, a family-friendly pool and beautiful garden. The place is situated in a secured gated community in lively Crown Point! We are also located close to the airport (5 mins drive), beaches (e.g. Pigeon Point - the #1 attraction in Tobago!), restaurants, bars, shops, grocery stores and ATMs (bank) for all your needs and amenities.

Top guest favorite

A spacious living area is characterized by modern furnishings, featuring a navy blue sectional sofa with decorative pillows. A coffee table sits atop a woven area rug, and natural light floods the space through ceiling windows, illuminating the open layout that connects to the kitchen.

Villa in Crown Point

4.98 out of 5 average rating, 49 reviews

Villa Blue Moon

Make memories at this unique and family-friendly place. A 4 bedroom 10 person villa located in secured compound close to beaches, bars and restaurants. With fun activities such as pool table, basketball, heated jacuzzi, swimming pool, 3 televisions, modern fully equipped kitchen, laundry room with washer & dryer, comfortable family room and Hi-Fi stereo system. A playful, open and entertaining home to feed your senses, to enjoy and unwind as you will

Top guest favorite

A private pool is surrounded by well-maintained greenery and decorative planters. The pool features a smooth edge with stairs leading into the water, and the bright blue surface reflects the sky above. A storage tank is positioned discreetly in the background.

Home in Bon Accord

4.97 out of 5 average rating, 110 reviews

Villa Magnolia

This cozy duplex is located just walking distance from both the airport and the world famous Pigeon Point beach. You can also enjoy several varieties of food just minutes away from this villa. Guests are sure to enjoy a memorable vacation in this fully furnished, cozy 3 bedroom villa, each with its individual bathroom with a powder room located on the main floor. The villa also includes a private pool.

Guest favorite

A bright living and dining area is featured, with large windows allowing natural light to fill the space. A comfortable gray sectional couch and a light-colored coffee table are positioned in front of a television. A dining table with chairs and artwork on the wall add to the inviting ambience.

Apartment in Black Rock

4.96 out of 5 average rating, 27 reviews

Sunset on the ocean

This apartment is unique in the Tobago short term rental space. Brand new, stylish "island chic" place offers ocean views and is right above one of the most stunning Tobago beaches. You have ample space for your family or as friends to enjoy spacious living and dining space, top of the art kitchen. The two bedrooms and 2.5 bathrooms give you the space to enjoy this calm yet very well located new spot.

Guest favorite

A serene pool area is surrounded by lush tropical greenery, creating a tranquil oasis. The clear water reflects the blue sky dotted with fluffy clouds. Comfortable seating options are located nearby, inviting guests to relax and enjoy the natural beauty of the landscape.

Cabin in Parlatuvier

4.94 out of 5 average rating, 109 reviews

Tamarind House Villa Parlatuvier

Tamarind House Villa is situated on the leeward coast of Tobago in the beautiful fishing village of Parlatuvier. It is suitable for small groups, couples and families who enjoy a relaxed lifestyle away from commercial tourist areas. The villa overlooks the bay on one side and pristine tropical rainforest on the other. Guests will have sole occupancy of the house, pool and gardens.